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Synlett 2010(11): 1589-1605  
DOI: 10.1055/s-0029-1219937
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Reactions of Chiral Guanidines and Guanidinium Salts

Dasheng Leowa, Choon-Hong Tan*b
a Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla CA 92037, USA
b Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Fax: +65(6779)1691; e-Mail: chmtanch@nus.edu.sg;
Further Information

Publication History

Received 9 February 2010
Publication Date:
19 May 2010 (online)

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Abstract

This account chronicles our discovery and development of catalytic reactions using chiral guanidines and guanidinium salts.

1 Introduction

2 Chiral Guanidines as Brønsted Bases

2.1 Synthetic Route for the Catalyst

2.2 Michael Reactions

2.3 Henry Reactions

2.4 Phospha-Michael Reactions

2.5 Diels-Alder Reactions

2.6 Protonation Reactions

2.7 Isomerization Reactions

2.8 Mannich Reactions

3 Catalytic Reactions of Chiral Guanidinium Salts

3.1 Michael Reactions

3.2 Phospha-Mannich Reactions

4 Chiral Guanidines as Ligands

5 Conclusions and Outlook

Key words

asymmetric catalysis - enantioselectivity - guanidines - hydrogen bonding - Michael additions

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